Travel and falling off your life wagon at 40

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Last Updated on July 29, 2014 by Christine Kaaloa

life past LA, how i fell off my wagon
Travel and falling off the life wagon at 40

 Los Angeles. I looked out at the smog-clouded city and its diorama of  street grids, freeways and moving car ants.  Giant Hollywood film billboards dot buildings as a reminder of an urban succubus, wooing millions of young, aspiring artists to live out their sparkle in the hope for fame.  This city would surely have more opportunities to work and travel than where I’m currently at. But in order to survive this city, I would have to adapt to the rules of its game.

What are the rules of the game when you’re single and starting over at 40?  

The last time I lived here, I was in my twenties, tangled in the mechanisms of an ill-fit youth, striving to be something I wasn’t. It was all too easy to be swept away by the glamoratzi image of the city– to party hard, be social, to see-and-be-seen.   Back then,  I was a whisp of a shell in search of a voice and I thought I could find my voice outside of me .

Since then, travel and life experience helped me find my voice. No problem there. Now I was searching for my shell.


Travel and falling off your life wagon

In an effort to finish this post, I pushed to find words until my brain hurt. Frustration. Silence. Still no verdict.

Delete. Trash. New post.  …And then I wrote this line:

”   Travel can clarify who I am.  It can also confuse it.    “

And here it sat on my blog shelf for two years.

Coming home after living abroad in Korea and months of backpacking wasn’t easy. With the employment shortage in Hawaii, my career revival wasn’t working out and I couldn’t find work in my industry or anywhere else, despite every effort. My past travel lifestyles and their proven track record of successes taunted me. It made standing still an excruciating torture.

•  You can have a travel job career, where you’re paid to be creative, do what you love and travel.

•  You can get paid to travel, live and work abroad.

•  You can travel abroad,  simply and happily on little money and with few possessions.

I wanted it all, fast and I wanted it bundled up in a job that would pay me to travel. Yet as I made this my new lifestyle manifesto, passionately investing all my time and energy working all angles to see which would adopt me first, something odd happened. The harder I pushed towards redesigning my life towards travel, the more constipated my life got. Nothing flowed. Even regular job opportunities passed over and around me as work buzzards circled overhead. Not even scraps.

Being a “gypsy traveler ” or “solo female backpacker” playing my hand at being hobo on the road is vastly different from the freezing cold reality of being nearly hobo in your own country! There’s nothing happy, winsome, sexy or liberating about being unemployed in America.

For the first time in my life, I doubted my ability to manifest a successful travel life . Answers eluded me as to how I could’ve fallen off my life wagon.  Was my life over at 40?

Was it time to put those dreams out to pasture and buckle down to a real job, with health benefits and where a suit behind an office desk asks you– Where do you see yourself in the next five to ten years?

Meanwhile, each time I took a step towards that idea,  my travel addiction worsened. It was my last saving grace and its affordability was drifting out of reach…

The meaning of shifting silences

Silence is loud if you actually stop to listen to it.


Delhi, India. It’s my third month in this country and the chaos of it is finally making sense!  Once foreign, this land of brilliantly-colored saris, spiced food and Hindu temples,  grows more familiar by the day.   Swaddled in the warm dust of chaotic streets, filled with sweat-pushed rickshaws,  drunkenly slow cows and zig-zagging bicycles, I flick my hand up and wobble my head, coarsely telling my Indian cabbie to “Chalo!” as we beep and rattle into the unknown.  It’s a mystery how I can push through my fears to navigate such chaos. But somehow it happens. I feel alive, like a heroine in an unfiltered reality. No safety nets here.  I’m moving through this big ‘ole world on my own, on travel steroids. A single woman. Content and happy. How did I do it?

 I put one step in front of the other, expecting the unexpected and went with the flow.

Flash forward to today.

Hawaii. Back in my parent’s house. Warm tradewinds saunter through mango trees to kiss my face. The Koolau mountains paint a majestic backdrop of the strong, but gentle beauty of Hawaiian island life.  I dine with a friend in a posh Honolulu cafe, ordering a $9 sandwich. Ouch, that’s a dent. Traffic is orderly and slow, but at $4/gallon it feels insufferable; it’s cheaper to not drive if you don’t have to.  Being in Hawaii can sometimes feel like living in a small town in Asia. People never speak what they think; instead the game is intellectual and coded in layers and sublayers. You must “know people”, wait your place in line patiently and know your place in the system. Say or do the wrong thing at work, burn a bridge and it’ll haunt your career for life; it’s better not to talk (or post these types of confessions on your blog).   How was I living it?

Just play by the rules, work hard, don’t lose your place in line and smile graciously. If you’re lucky, maybe you’ll get your big break at 50!

travel inspiration, motivational, womens inspiration
The strength and lessons you find in solo travel

The only certainty is uncertainty

Life doesn’t get easier, the older we get. That’s just the basic assumption.

Life feels clearer the more I learn about myself, but it also feels more complex. Time, age, gender, finances, relationship status and all the imagined tripwires and societal pressures complicate my free movement.

We grow, outgrow, change identities and dreams.  And yet, we still expect to have our lives figured out  by age 20, 30, 4o, 50,…

Like clockwork, every ten years I find myself at the same crossroad, where I must choose between the safe path or the crazy path of my wildly-beating heart.  Nine times out of ten, my heart addiction wins and the only certain path is uncertainty.

Like everything, I weigh the pros and cons of where I’m at in my life versus what I want. My pendulum shifts– Move abroad or stay in the United States?  Fight for an old career or get a new one? Gamble on myself to win or play it safe?  


Sometimes, discomfort is necessary to propel you forward.

When life shuts you down in all directions, you begin to look at solutions you might never have thought to try.

A river’s flow doesn’t stop just because it hits a wall. On the contrary, it goes over it or around it, finding crevices and cracks to continue its journey. Maybe that’s the other definition of ” following your destiny”.

travel inspiration, motivational
When life shuts you down in all directions, you begin to look at solutions you might never have thought to try

Stubbornly, I want it all- my dreams, simplicity, a career in entertainment, financial growth… and yes, a job that lets me travel. Each part of the pie completes me.  Separately, each will leave me less than full. 

I long to travel the freedom and ease of an open road, an impromptu itinerary and a place, where not having answers makes sense, amidst foreign stares.  I yearn to be lost and nameless, but to be an adventurer, who gains strength in the ability to survive on foot in a huge world.

And yet,  I also long for the warmth of chains, to climb high-rise dreams like a mountaineer, to make a name for myself and to experience the challenge of living in western society, where like a gladiator, I gnash and gnarl at things, to test how good I am at getting them … and yes, at 40.

|   I love this struggle of life . At the same time, I hate it.   |

And that has a silent ring of being my truth.

In my case, who I am is not an “Either / Or” decision.  My challenge is to find a comfortable balance for doing all the things I love, while I experience travel and explore the mystery of life around me.

Yes, travel pushed me off course, when I defined my happiness as a single plane ticket to escape the boredom of my life. I wanted it to be a cure-all shell to live in, so I wouldn’t need to deal with choices of how I could make the rest of my life’s needs and passions work. Meanwhile, those passions allow me to see and feel travel in the variety of life forms around me, …in challenges, people I meet and places I visit in order to create a bridge over bi-polar dreams.

It occurs to me now, that I didn’t really fall off my life wagon. I’ve riding on it all along… a traveler of my own life.

I’m putting one step in front of the other, expecting the unexpected and going with the flow.

How about you? Are you longing for a bit of gypsy freedom, which makes your heart beat with the wind; while desiring an ornate bracelet of chains and wedding rings?


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Blogging, Gap Year Travel, Inspiration, SOLO TRAVEL


  • Being at the crossroads is a good thing! It means we have options. It means we are conscious, thinking humans who realize our time here is limited and want to ensure we make the most of it.

    Life is so much more rewarding when marching to your own drum beat. We’ve got to follow our hearts and do what we feel, or else we’re just enduring, that’s no fun.

    I don’t buy it when people say “well that’s life, it’s what EVERYONE does.” It’s a cop out. Stand against society and do what you desire, it will all be over in the blink of an eye anyway.

    Personally, I turn 40 in January and am leaving behind a great job and selling my stuff to have a life of more freedom. No wife, house or kids by choice. Time to explore, work on freelance more and have an open ended time table.

    First stop, Goa India!
    Keep it up Christine.

    • Christine Kaaloa
      September 10, 2014 4:02 pm

      @Jeff: Awesome and congrats on taking the leap! It’d definitely a period when you focus on making your time and actions count! Good for you for following your dreams.

    • Christine Kaaloa
      September 10, 2014 4:03 pm

      p.s. @Jeff: I love India. Hope you enjoy it- try to get around India… each region has it’s own culture and terrain.

      • I hv been following your india trip on you tube. rightly said….each area has a culture of its own. Would avoid Bihar…thats it. Originally from India and travelled allover the country. ..guess…avoid that state (being a new comer)

  • Hi Christine! I love this post! Like most of those who have replied, I am also trying to find that balance. In doing so, I still sometimes feel like I have fallen off the life wagon (such a perfect way to put it!) I think you get used to the life you end up with, and even if it is uncomfortable (like that itchy tag in your t-shirt), it is familiar. It’s what everyone around you is doing. To go after the life you crave is usually a daunting task: facing the unknown, going against the norm, trusting in yourself and what you know is right for you.
    I came to Korea to teach English about 2 years ago, but it took several years of dreaming, wishing, not really believing… to get to that point. I’ll be traveling solo for the first time this November (at age 48!) I am so excited and of course, nervous! But your blogs have been encouraging and inspirational.
    “It occurs to me now, that I didn’t really fall off my life wagon. I’ve been riding on it all along… a traveler of my own life.” Exactly!!

  • I’m glad to hear that I’m not the only one who struggles with this. I’m not yet thirty but getting close and haven’t yet found the courage to let go of the life I have always know. It’s getting to the point that I feel if I don’t do it soon I never will. That though is honestly starting to scare me more. I’ve started with HubPages and have been looking into other forms of work so that I can fund what I want to do, but it can be a bit confusing to navigate it all at once. I have actually been considering moneyless travel but I’m not sure if that is a route I want to go. At this point all I know is I’m stuck.

  • Sound Great that you get to travel all over. Other than the US I really didn’t travel to many areas. Last year I went on a tour (solo) of Europe (luckily I had a lot of airline miles to use) and this coming November I am travelling to Japan with a few days in Seoul, also using airline miles. Kind of scary, even though I’m a guy I can’t speak the language so a little unsure of getting around, especially going solo. I had some difficulty in Paris (ugly American I guess) because I didn’t speak the language. Many parisians weren’t very friendly (even though I smiled and said bonjour), some actually gave me the wrong directions, one guy had me take the wrong train, luckily I looked at the stations on the train and got off and backtracked and found the right train to get to my destination. He probably did it on purpose because he would know how to get to a popular area of paris, he probably through it was funny to misdirect the American tourist.

    Anyway, it’s neat that you are independent (and brave) enough to travel all over the world. Great that you are getting it out of your system while you are young, when you are older it is harder and you get more into a “routine”.

    From one Hawaiian to another.

    • Christine Kaaloa
      August 22, 2014 5:01 pm

      @Stan: Looks like you’re changing your travel life! Congrats. Parisians can be pricks. ha ha. I’ve heard the thing about telling tourists the wrong direction too. I didn’t experience that- partially because back then I had a gf who spoke french and I hobble along with the French language myself b/c I love the culture. I also play up a cute dorky face when I know I’ve got it wrong- it disarms folks! 😉 Navigating foreign languages can feel tough, so it’s helpful to be armed with a few survival phrases- I feel like locals appreciate the effort. The stereotypical American won’t try to learn any language or adapt and that’s what I think French hate… kinda like mainlanders or military not adapting to our HI culture. Same sentiment. Japanese and Koreans are much better. They’ll appreciate your trying, miming and I find they’re helpful with directions. Take a survival book or a phrase app if you’re uncertain. If a direction you’ve been given *feels* wrong, ask for a second opinion. Usually, your gut is right. Miming is a fun way to make others laugh and play with you.

      As for “getting to travel”- movement has always been a fact in my life. Fortunately, I’ve always found work that integrates travel, but Hawaii is a harder beast in that regard. A routine is actually painful to me, so as a survivor, I look for ways around having to encounter it. In 40+ years, the closest I’ve come was a 9-5 job was teaching in Korea.

      • It helps to be female (not as intimidating) and gorgeous as you (hey, not fair). Hard to be rude to someone with your all American smile, lol. I did try to speak a little French (parlais vou…. sorry butchering the language) but I think Parisians don’t like it if you don’t speak their language or butcher their language, one guy said I should stick to English, lol.

        Gosh I could never see myself in an 8 – 5 job but I’ve been doing it for over 30 years already. At least I can see the retirement light at the end of the tunnel (6 to 12 years) and for now I’m getting the travelling out of my system (my friends want me to go to Thailand with them for…you know what…but I rather also do other things when I go to other places) when I can afford it. Just wish I had someone to travel with, hard to navigate when going solo IMHO. Have a nice day!

  • I understand all you are saying even if it’s not all rational. Life is complicated and it is easy to get bored, no matter how good things are. We had a good life at home but our society is complicated and we felt tied down and feeling in some ways that we were just feeding the system. We’ve slowly gotten untangled from things over the last few years and finally packed up everything for life on the road. Still working from a distance but we feel at least 50% freer that we did. Its a brand new start and a transition to a 100%-work free life that we hope to achieve within the next year or so. Things tie us down in our societies; owning a house, working 9-5. Even little things like being tied down to a cell phone contract. Now on the road, paying cash as we go along, having little in our name, being able to go where we want, when we want is an incredibly liberating feeling. It’s the life we’ve always wanted.
    Yet at time I feel what you’ve described; the need to go back and pursue a career and to challenge yourself in that way. Then I have to pinch myself and remember that I spent 20 years doing that and that I have nothing to prove. And how sick we got over the whole rat race. But its like our lives and society don’t want to let us go and keep pulling us back. In reality it’s just our minds bringing us back to what we used to, where we felt the most comfortable. Transition is hard and takes a while, and it DOES get harder when you are older. And when I sit down and think logically about it I realize that we have to move on, that we would never be happy going back to our lives as they were.

    So I think I get what you are saying above, I think some of your feelings may be similar.

    Frank (bbqboy)

    • Christine Kaaloa
      August 5, 2014 4:06 pm

      Yes, @BBQboyFrank. I’ve totally experienced what you’re saying about feeling tethered to the unhealthy parts of society. That’s a big compromise to deal with when you’ve tasted travel freedom. Living abroad taught me what it’s like to live organically on my own terms and everything you’ve mentioned. (I can’t stand having a cellphone contract- btw) And yet, even as I lived abroad, I’d occasionally feel haunted by those personal dreams I’d never be able to pursue.. I’d find myself wondering — could I let go of my (other) dreams and not feel any regret in the long run? (those dreams are far from comfort zones actually- they’re very uncomfortable pie-in-the-sky ones! he he). I’m passionate about travel, but I had to ultimately ask myself: if it was fulfilling for me to travel for “travel’s sake” or more important for me to travel for a creative purpose.

      Personally, my creativity has since birth, been my demon/mistress and liberating her so she can play and be brilliant, is ultimate freedom to me. When I was in the rat race, I didn’t leave a job I hated or felt enslaved by. I was in an entertainment travel job I loved, demon girl was doing cartwheels of fun and thrills, and yeah, I had to deal with some stinky people along the way. I had to pay rent, afford medical insurance, worry about my next job, fight with service providers about them overcharges, deal with work politics.

      But had I remained living/teaching ESL in Asia (my very first 9-5 job), I know in time, it would surface a stinky society to navigate as well. Rent, cellphone plans or sim cards, how to survive economically, dealing with difficult work colleagues and difficult cultural barriers… I’d only be running back to the very society-based system, I tried to escape. The only way to conceivably avoid enslavement is to live continually on the road… and if you do that, I find that incredible and say, rock on! Because not every personality is capable of that. =)

  • LOVE this post. I’m at a point in my life at 49 when I want to move on to new opportunities after being at my current job for 23 years. But, I don’t yet have my “pegs” in place; I haven’t done enough legwork. I also have commitments at home that I can’t just leave behind. So, for the time being, I’m sticking it out, doing the best I can at work while realizing that laziness is the enemy and I need to take action to line things up in order for me to hopefully find paths opening up down the road. Hoping you get the Travel Channel opportunity—that would be so amazing! Thank you for your thoughtful and candid post.

    • Christine Kaaloa
      August 5, 2014 3:21 pm

      @Sarah: One problem I find with the travel community is that you have all these stories where people “escape their lives” and just “leave everything behind” and that’s supposed to be a glamorous thing. For some, that appears to be a cure-all; but I’ve found, the problems don’t leave; they just find ‘different faces’. Being a travel blogger is another word for being a freelancer; you’re developing a business and it has long hours and uncertain pay, which is fine if you live in a cheap country. ESL teaching for a small salary is great, but what happens if you ever decide you want to come home? I was talking to Tom Gates, Kvlogger of @SeoulTee about being 40s; the consensus was the older you get, the more you try to make decisions that count towards your future. You squander less and as time ticks, it’s necessary to pull out the stops and go for it. You don’t have to cut all cords to your life back home to have your dream and not all pegs have to be in place for you to start. I’m a prime example of not having *any* pegs in place, while still getting that Travel Channel opportunity. Define your vision, start working your way towards it and let obstacles give you a guiding hand, showing you things about yourself and your dream, you may not know.

      • You totally hit the mark! And the consensus is right on. True about the pegs…I guess the main thing is to keep the door open to any opportunity, and even if it doesn’t fit into my idea of what it should be, that doesn’t mean it won’t take me somewhere I need to go. Thank you for your thoughtful reply.

  • Hey Chris, love this post. So insightful. Keep on writing!!!

  • I love how you said travel helped you find your voice, but now you’re looking for your shell. Nicely put! It’s tough being one part spirit/idea/possibility, one part body/grounded/logic, but navigating that tension seems to be our role as humans. When you figure out the balance, let me know lol!

    • Christine Kaaloa
      August 5, 2014 2:46 pm

      @Jenna: Yeah I think you’ve nailed it- the part spirit, part body thing… a long-time human struggle. If I find that delicate balance, I’ll definitely let you know! Although I think you’re doing pretty ok!

  • I enjoyed this post. I’ll be sure to read and follow you. I’m finally coming into my own in my forties where everything is clicking. It’ll happen for you too. Travel is the ultimate metaphor for life.

    • Christine Kaaloa
      July 31, 2014 1:06 am

      Yes, @Pete, wonderful to hear things are clicking for you…”coming into my own” is one of the nice things about crossing into your forties.

  • Well said. Life is an ever changing journey and one never quite knows where they will end up. And just so you know, I’ve found the 40s to be the best time of my life – full of new directions and opportunities. I’m sure it will be the same for you.

  • Wow Christine – I couldn’t have said it any better! I discovered solo travel last year with 3 weeks in Japan, followed up with 2 weeks in Korea this summer. I am also starting over … at 52. I always chose the safe path before, but found with my first adventure in Japan that Plan A doesn’t always work out – yet Plan B might be even better! I’ve fallen in love with the the idea of adventure solo traveling – planning a “gap year’ myself, maybe only in my fantasy life. I found your site while in Korea researching things to do and see and eat. Going back and forth between getting a desk job with benefits, which makes me nauseous, and the uncertain path of doing the things I love, which makes my heart race. Have decided to give it a go at what I love, because I have a new confidence from my solo travels. Love your blog – keep writing!!!

    • Christine Kaaloa
      July 31, 2014 1:03 am

      Thanks for sharing @Michelle and going solo at 52 is awesome! Solo does make you bolder and it’s interesting how plan B seems to work better than A. Used to have this saying when I was an artist– mistakes are a blessing to excellent art… never take the first idea. I feel like balance is the key, as are ways to fluff your passion or challenges when things get stale. There’s a TV cameraman I occasionally assist who’s been working on the same HGTV house show for over 10 years. It’s a popular show, but other cameramen might look at that as the equivalent of the nauseating boring office job. Still, he’s always working and constantly reinvigorates himself with challenging himself to find creative shots. With the right frame of mind, you can will anything you want! =)

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